5-alpha-Hydroxy- Laxogenin Chemical Properties

Melting point:

247-250 °C

Boiling point:

578.4±50.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMF: 15 mg/ml; DMSO: 10 mg/ml

form 

A solid

pka

12.62±0.70(Predicted)

InChI

InChI=1/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)12-20-18-11-22(29)26(30)13-17(28)6-9-25(26,4)19(18)7-8-24(20,23)3/h15-21,23,28,30H,5-14H2,1-4H3/t15-,16+,17+,18?,19?,20?,21?,23?,24+,25-,26+,27?/s3

InChIKey

HCRGPOQBVFMZFY-YPAZECSTNA-N

SMILES

C1C[C@]2(C)C3CC[C@]4(C)C5[C@H](C)C6(OC[C@H](C)CC6)OC5CC4C3CC(=O)[C@@]2(O)C[C@H]1O |&1:2,7,10,15,27,30,r|

5-alpha-Hydroxy- Laxogenin Usage And Synthesis

Uses

5α-Hydroxy laxogenin is a synthetic derivative of a naturally occurring spirostane-type steroid, laxogenin. It is a synthetic spirostane-type steroid, which is contained in dietary supplements and advertised as anabolic agent. 

Description

5α-hydroxy Laxogenin is a brassinosteroid analog and a derivative of diosgenin.Topical administration of 5α-hydroxy laxogenin (4, 8, and 12 ppm), in combination with a commercial fertilizer, increases the yield and fresh weight of endives (C. endivia).It also inhibits sodium chloride-induced decreases in the fresh weight of lettuce shoots and roots when applied topically at concentrations of 0.1 and 1 μM, as well as inhibits increases in ethylene emission at a concentration of 1 μM.

Synthesis

5 g (10.2 mmol) of compound 8 (CAS:5874-17-9) was taken as raw material and dissolved in 390 mL of methanol. Subsequently, a solution of 4.6 g of NaHCO3 dissolved in 60 mL of water was slowly added and the reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and left to settle. The settled reaction mixture was poured into water, filtered and dried to give 4.35 g of the target product S9 (95% yield) with a melting point of 272 °C (methanol). The structure of the product was confirmed by the following characterization: IR (KBr, cm-1): 3396 (νOH), 2953 (νCH), 1703 (νC=O), 1449 and 1380 (δCH), 1055 (νC-O), 977 (spiroketal); 1H-NMR (δ, ppm): 1.97/1.30 (m, 2H, H-1). 1.80/1.45 (m, 2H, H-2), 3.93 (m, 1H, H-3), 1.84/1.69 (m, 2H, H-4), 2.82/2.04 (m, 2H, H-7), 1.94 (m, 1H, H-8), 1.99 (m, 1H, H-9), 1.51/1.36 (m, 2H, H-11), 1.81 /1.28 (m, 2H, H-12), 1.47 (m, 1H, H-14), 1.96/1.29 (m, 2H, H-15), 4.44 (m, 1H, H-16), 1.83 (m, 1H, H-17), 0.82 (s, 3H, CH3-18), 0.83 (s, 3H, H-19), 1.90 (m, 1H H-20), 0.99 (d, 3H, CH3-21), 1.70/1.60 (m, 2H, H-23), 1.65/1.46 (m, 2H, H-24), 1.64 (m, 1H, H-25), 3.48/3.40 (m, 2H, H-26), 0.82 (d, CH3-27); 13C-NMR (δ ppm): 30.4 (C-1), 29.8 (C-2), 67.2 (C-3), 36.5 (C-4), 80.7 (C-5), 211.7 (C-6), 41.9 (C-7), 36.7 (C-8), 44.6 (C-9), 42.4 (C-10), 21.3 (C-11), 39.5 (C-12). 41.1 (c-13), 56.1 (c-14), 31.6 (c-15), 80.5 (c-16), 62.0 (c-17), 16.4 (c-18), 14.2 (c-19), 41.6 (c-20), 14.5 (c-21), 109.3 (c-22), 31.3 (c-23), 28.8 (c-24), 30.3 (c-24), 30.3 (c-24), 30.3 (c-24), 30.3 (c-24), 28.8 (c-24) 24), 30.3 (c-25), 66.9 (c-26), 17.1 (c-27).

References

[1] Molecules, 2016, vol. 21, # 8,

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